Bromine → HCID 57685251, compound

HRID 1671820Notes

Reaction equation

HRID 1671820 reaction equation
FC1C=CC=CC=1C1C=CN(C)N=1.[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[N:25]([CH3:26])[N:24]=[CH:23][CH:22]=1.[Br:27]Br>C(Cl)(Cl)Cl>[Br:27][C:22]1[CH:23]=[N:24][N:25]([CH3:26])[C:21]=1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[F:14]

Participants

5

Reactant 3

HCID 24408BromineHCID 57527163HCID 57527163, compoundHCID 57527236HCID 57527236, compound

Product 1

HCID 57685251HCID 57685251, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

To a solution of a mixture of 3-(2-fluorophenyl)-1-methyl-1H-pyrazole and 5-(2-fluorophenyl)-1-methyl-1H-pyrazole (6.77 g, 38.4 mmol, 1.0 eq.) in chloroform (10 mL) under nitrogen at 0° C. was added a solution of bromine (2.0 mL, 39.0 mmol, 1.0 eq.) in chloroform (5 mL) over 10 min. After 50 min, the reaction mixture was diluted with chloroform and washed with saturated aqueous NaHCO3 (3×), dried over Na2SO4, filtered, and concentrated in vacuo. Silica gel chromatography using hexanes:EtOAc (10:1) as eluent afforded 4-bromo-5-(2-fluorophenyl)-1-methyl-1H-pyrazole as a white solid (2.70 g, 28% yield), a mixture (0.65 g, 7% yield) and 4-bromo-3-(2-fluorophenyl)-1-methyl-1H-pyrazole as a white solid (5.94 g, 61% yield).

Workup

  1. washwashed with saturated aqueous NaHCO3 (3×)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b412eedd8f5443cea681626efe08415f
Source dataset
uspto-grants-2011_08
Patent number
US07994337B2

Reaction notes

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